91763-35-8Relevant articles and documents
Rhodium-Catalyzed Alkenylation of Toluene Using 1-Pentene: Regioselectivity to Generate Precursors for Bicyclic Compounds
Liebov, Nichole S.,Zhu, Weihao,Chen, Junqi,Webster-Gardiner, Michael S.,Schinski, William L.,Gunnoe, T. Brent
supporting information, p. 3844 - 3851 (2019/10/16)
Rhodium catalysts for arene alkenylation reported by our group (e.g., Science 2015, 348, 421; J. Am. Chem. Soc. 2017, 139, 5474; J. Am. Chem. Soc. 2018, 140, 17007) have demonstrated selectivity for 1-aryl alkenes over y-aryl alkenes (y > 1). This selectivity is notable because 1-aryl alkenes or 1-aryl alkanes cannot be generated using acid-based Friedel-Crafts arene alkylation or acidic zeolite catalysts. Herein, we report the extension of Rh arene alkenylation catalysis to generate 1-tolyl-1-pentenes, which are potential precursors for bicyclic compounds. The olefin concentration, copper(II) oxidant identity and concentration, reaction temperature, and rhodium concentration for the alkenylation of toluene with 1-pentene have been optimized using [Rh(Η2-C2H4)2(μ-OAc)]2 as the catalyst precursor. The rhodium-based catalysis achieves up to 12(1):1 anti-Markovnikov selectivity for 1-tolyl-1-pentenes over 2-tolyl-2-pentenes and is selective for alkenylation in the meta and para positions.
The carbonyl group tuned electron-deficient phosphorus ligands and their application in Rhodium catalyzed arylation to aldehydes
Yang, Jiefang,Chen, Xingyu,Wang, Zhiqian
supporting information, p. 5673 - 5675 (2015/09/15)
Acylphosphines, which could be efficiently prepared from acid chlorides and secondary phosphines, were developed as a type of carbonyl group tuned electron-deficient phosphorus ligand. They were found to be a kind of efficient ligand in Rhodium catalyzed arylation to aldehydes through accelerating the transmetalation process. Chiral acylphosphine ligands could be generated from carboxylic acids bearing the chiral framework correspondingly.
Iron-catalysed, general and operationally simple formal hydrogenation using Fe(OTf)3 and NaBH4
MacNair, Alistair J.,Tran, Ming-Ming,Nelson, Jennifer E.,Sloan, G. Usherwood,Ironmonger, Alan,Thomas, Stephen P.
, p. 5082 - 5088 (2014/07/08)
An operationally simple and environmentally benign formal hydrogenation protocol has been developed using highly abundant iron(iii) salts and an inexpensive, bench stable, stoichiometric reductant, NaBH4, in ethanol, under ambient conditions. This reaction has been applied to the reduction of terminal alkenes (22 examples, up to 95% yield) and nitro-groups (26 examples, up to 95% yield). Deuterium labelling studies indicate that this reaction proceeds via an ionic rather than radical mechanism.
